


Diary of the Breaker Queen

by WanderingOwari



Category: Original Work
Genre: Alternate Universe - Gangsters, Alternate Universe - Urban Fantasy, Crossdressing Kink, F/M, Heartwarming, Impregnation, Mafia-style, Massage, Missionary Position, Oral Sex, Slight worldbuilding, Threats of Violence
Language: English
Status: In-Progress
Published: 2020-10-01
Updated: 2020-10-01
Packaged: 2021-03-07 22:01:06
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,303
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26754724
Author URL: https://archiveofourown.org/users/WanderingOwari/pseuds/WanderingOwari
Summary: EDIT: (formerly 'A Night to Unwind', I might change this from a simple one-off to snippets/stories featuring this peculiar series)The all-powerful 'Breaker Queen', head of her own crime syndicate, the 'Breakers', and the many snippets/aspects/eventful moments in her life!
Relationships: Original Character(s)/Original Character(s)
Comments: 2
Kudos: 7





	Diary of the Breaker Queen

**Summary for the Chapter:**

> The Queen, after a stressful day, gets a much needed massage from her favorite floozy... which in turn stirs up a question, and the inevitable issue of succession...

The entire West Coast was in her hands.

Strong and sturdy men as her enforcers, her hooch-runners, her drug-dealers...  
Whimsical young lasses, sneaky as they were nimble, her scouts and informants, her street workers and assassins...  
Disciplined, powerful women, acclimatized to strengthen her forces and their resolve...  
And with the possession of mystifying artifacts, even hulking ogres from the Orient, and minor emissaries of the elements, served under her, to keep tensions high and circumstances mysterious amidst the populace and authorities...  
And even better than that, even the cops couldn't stand up to her or her goons. Especially since some of their best and brightest were under HER employ, working to undermine local authorities while consolidating power for HER...

'The Breaker Queen' was the uncontested matriarch of the Breakers, the biggest crime syndicate this side of the West Coast. No one truly knows how vast her empire truly was, to what extent she owned the United States. Rumors has it that she might actually own the entire western half of the country...!

All that was known was that she was a woman who was so easy to spot, you couldn't miss her even if you tried: a young albino woman with flowing snow white hair and striking ruby eyes. She dressed like a typical gent in a dressy button-up black pinstripe shirt and vest, complete with slender black slacks, sharp heels, and a peek of nylons adorning her legs. The suit did nothing to pin her stellar, shapely bosoms down, nor did it slow her down when she would dole out some 'enforcing' of her laws personally--whether it was to officials who didn't comply to her syndicate's demands, or punished goons who thought to undermine her simply because she was a woman.  
  
A young woman--who would brutalize **anyone** who dared to ask her age-- who was also a scrapper; to tell her to stay out of the crossfire and let her forces handle things would be met with deaf ears--many times in her life, she would charge into raids and shootouts alongside her people, even if it meant a target being planted on her back or chest. And in her strong gloved hands--hands that radiated immense heat or intense cold--she would enact her will and punish anyone who defied her without question! And one who defied the phobia that people of her skin-tone would burst immediately into flames if exposed to the warmth of the sun, and beat that statement into any who mocked her for it.

Her hometown of Elsewhere, the place she was born, was where The Breaker Queen started her criminal empire. It would be Elsewhere that would be the seat of her Empire, and it would be Elsewhere that she would enact her plan to ensure that power would remain here in her home, and that her rights of succession would remain 'in the family', so to speak...

\--

"Mmmm, doll, you always know where to put those magic fingers of yours to work..."

"A tough day teaching mooks a lesson and putting that baka Chauncey in his place--you deserved that nice soak and my magic fingers, boss-man."

The Breaker Queen sighed contently. Her home was a lavish two-story mansion; what was once run-down and in squalor as a child, it was remodeled and had new life breathed into it. The ground floor was for her people who needed a quick place to hide out for the night, to get away from bothersome spouses, to find shelter from their enemies and abusers... as long as they behaved and stayed out of the top floor--unless there was quite important and IMMEDIATE business that warranted The Breaker Queen's attention--they were always welcome.

The top floor, of course, was HER domain. Her private study. Her office which she carried out the administrative and clerical duties of her syndicate. Her parlor where she could watch the news, or unwind with a radio drama and a hot cup of tea. Her master bedroom and adjoining bathroom that made her look like royalty--which was entirely fitting, after all. And of course, a place she shared with her molls. Many dashing gentlemen and comely lasses had come and gone in her life...

But this one... THIS cutie was different and she knew it. A cute, short-haired brunette she got from an associate from that way-off country called 'Japan'... there was something about this lady-boy that tickled her fancy. Younger than her by a year or two--who was counting?-- effeminate, practically hairless all over, soft chocolate eyes, looked good in all the clothes, undergarments, and scandalous fare that all the racy flappers and call-girls donned, packed something suitably fitting below the belt, and had a spark in him that ensured that he wasn't a complete weakling or pushover.

Correcting and rebuking one of her disciplinarians for calling him a _Chinese_ lady-boy instead of his true nationality when she first laid eyes on him... Oh, he still got the tar slapped out of him by the Queen herself for forgetting his place, but without knowing it himself, he had been 'chosen' by her.

Chiyosuke Keimaro was his name. A hodge-podge of a name, both masculine and feminine. 'Chiyo-chan' was the name he preferred when he was with the other molls, or when he was serving the Breaker Queen as the one who relieved her tensions, who made her sigh with satisfaction at the end of a stressful day, and whose hidden firebrand personality had once saved her from a break-in--an assassination attempt on her life at the risk of his own! Oh, she would have to ask him what he himself was potentially keeping secret inside himself...

It would be the first time that the Breaker Queen had chosen a **favorite** among her molls. Chiyo-chan could stay with her in her 'inner sanctum' without question. Many had suspected ulterior motives--perhaps having to do with his situation? There were even allegations that he was a spy for a highly-vaunted crime family across the ocean. But the lady-boy had no family back home, no place to go except for Elsewhere, and no motivation to want to try anything underhanded against the Queen herself. In the day time, he would amuse himself and keep her mansion tidy like a good lady-boy would. Many nights, she would have him in her bed; when she was away, he would keep her sheets warm and yearn for her strong touch and 'comforting' presence--the latter being something unfamiliar to her goons...

"Tell me, my doll," her eyes glanced back at him in the middle of his firm physical 'therapy', "how long have you been my moll?"

The brunette hummed faintly, lost in thought as his fingers kneaded her bare shoulders; these massages after a hot bubble bath she'd take were the best times to work her cleaned, tired, towel-clad body into supple submission. "Four years exactly, to the date, boss-man."

"Hm? Only four, Chiyo-chan?" She asked, eyes lost in her bedroom, before focusing on her mirror, seeing her damp hair resting on her shoulders, as well as her brunette beauty clad in a soft cream nightgown, white undergarments, and a matching garter-belt and nylons. Cream and white suited him well in the bedroom--she was glad he picked these colors for tonight. She was a little disappointed he opted out of applying make-up tonight; his cosmetic touch made him look RADIANT. "Mmmm, how DOES the time fly, doll~?"

"Well, time flies when you're working hard, boss-man." He affirmed, catching her groan when he rolled the balls of his palms along her shoulders. "Mmmm, so tense... I might need you on your stomach so I can do your back."

"Mmm, if that's what my little therapist demands..." She intoned teasingly, before she slipped around and laid on her stomach on her bed, her towel covering from beneath her shoulder blades to just above her knees. She sighed when she felt him straddle her lower back, then felt those strong and sensual fingers work on her shoulders some more. "Ooh, Chiyo-chan, that hits the spot...!!"

"So much tension there... I can't have that on my boss-man's body, no sirree~!" He giggled delightedly, before Chiyo's fingers resumed their duty of easing tension out of his boss. "Mmmm, so milky-soft... have you been using my bubble-bath by chance, boss-man?"

"Mmmmn, I have, doll. I hope that's not a problem... After all, YOU are _mine_ , and what's yours is _mine_... and that oughta include the secret to your perfect skin, toots~!" She cried out when she felt him dug his fingers into her hand, feeling him shift from fingers to his knuckles. "Ah, holy shit...!"

"Mmm, the jig's up... Sore ga dou naru ka~" Chiyo kneaded her back, before he shimmied down her body to work her lower back next, getting another satisfied sound from her.

"Oooh, the way you still know that 'Tokyo-talk' after all your time with us," the Queen mused and sighed, "mmm--how do you do it?"

"...You DO have a fair number of oni in your employ, boss-man." He answered matter-of-factly, letting his finger trail whimsically down her back. "They are beings from MY home country. We DO talk here and there, ne~?"

"Mmmm--my sexy smart-ass~ I oughta have you just shoot the breeze one boring e--eeeevening, say whatever you want, while I don't know--mmmnnn--a lick of what your saying...!"

"I could, but I know that's not what you're craving tonight... But I'm gonna keep it in mind, Breaker Nishi-no-Joou~!" Chiyo's fingers had finished working their magic on her back, yet instead of pulling up and off of her, his fingers shimmied down to the bottom of her towel.

The Queen's eyebrow had perked from the feeling of her lady-boy compromising her 'modesty', but then bit her lip and, failing to hold onto that sense of modesty, moaned out from a very familiar sensation invading her from below. His lithe digits kneaded and toyed with her ass-cheeks, her glutes, easing her into having her rear in the air, so he could obediently make a slip of the tongue along her nethers.

"Mmmmnnn, y-you're a naughty dame, Chiyo-chan...~" She cooed out, her fingers gripping the bedsheets beneath her, while nuzzling her hips against his face. His lips and his tongue had always done wonders to her mood, no matter where he applied them. Those lips were always delicious to taste and claim, especially as her tongue shoved firmly inside his mouth to assert her dominance over him daily; her heavy breasts got so tight and stuffy beneath her suit day-in and day-out, and he would always be happy to give them a much-needed massage by request, kneading and suckling on her to ease her tension...

And much like this very moment, his tongue invading her snow-framed pussy was a wondrous blessing, a reward for running her criminal empire well everyday. Hands kneading that ass of hers, lips kissing and pressing into her muff made her more damp, and his tongue thrusting past her pussy and into her vagina proper made her caterwaul like a feline on an alley fence. His fingers, that wet muscle, it made the woman sing out loud in blissful pleasure--even if she only humored the thought of singing to herself on bored days when no one was around.

Her toes curled from his assault, her fingernails dug into the sheets, and she felt like budging an inch would ruin the feeling of his soft lips against her puffy nethers, or even throw off the pulse, push, and thrust of his tongue inside her heated canal. And to hear his own satisfied moans, which in turn sent pleasing sensations into her flesh, sought only to make her sing like a lust-starved canary! Her mind was screwed, shaken like a cocktail mixer, finding no purchase to even voice out his name, leaving her only to gasp, cry, and squeal airily for her favorite moll.

She bit her lip hard, yet the Queen failed to suppress her cries, as she crested and came hard, drenching his lips and glazing his tongue with her essence. His lithe hands kept her ass up in the air to keep her from slumping forward, her breathing ragged as she fought to keep herself composed after a mind-boggling orgasm. All she could experience was the sound of her moll cooing in satisfaction, of his tongue lapping her soaked cunt clean, and of his fingers giving her rear one last patting, before he slipped away and she caught him at the foot of the bed from the corner of her eye.

"Mmmmn... feeling relaxed now, boss-man~?" Chiyo asked her.

"Aaahh... That tongue of yours--it's fucking magic, isn't it~?!" She let out as she finally turned to lay on her side, her eyes on her dainty-clad moll's body, before looking past him and to her drawers. The correlation could be seen in her eyes, the slight upward twinge in her lips. "The sinful black, doll."

His eyes widened with a genuine surprise, followed with a practiced gasp. "Celebrating something, boss-man~? I ain't complaining, but you only wear your sinful black lingerie when you got something cookin' in your head..." He slinked over to her dresser, fingers finding the right drawer and pawing for only the most tasteful of her undergarments. "Like when you came up with the 'Diamantoupolos Murder Plot' and took all of Los Angeles for yourself...! Mmm, those bakayarou didn't even see it coming~"

"How right you are, my exotic doll~" She purred, shifting to sit on the edge of her bed. "And I'll let you know what I'm thinkin' of in a minute. Now quit the yappin' and fetch me the goods, or else I'll tie you to the bed again, and I WON'T be Miss Nice Guy this time~" She 'threatened' with a starved lick of her lips.

Thankfully there was no further delay from her spritely doll, the articles so closely kept to his chest, while he himself looked so sinfully pure yet corrupt in cream and white lingerie--especially so with his panties pitching a tent that hadn't yet drooped from lack of attention to it.

She threw the towel off of her body, and let her most sensual, most private ritual between them begin.

She lifted a leg out, and he would peel one article from the sensual pile, a sheer black stocking, and she would watch him slither the article up her leg, inch by agonizingly smooth inch, peppering painted kisses up her leg until he reached her creamy white thigh and set the hosiery in its clingy place. And as expected, a repeat performance of delicate decadence was repeated for her other leg. A lacy black garter-belt capped this miniature ceremony, hugging her waist while the suspenders clasped those delicate stocking tops that hugged such strong, porcelain-white skin so closely.

Many of her people underneath her--including her underlings, entourage, and family--assumed that such a strong, powerful woman didn't enjoy such delicate articles clinging to her body--too effeminate for her, too 'contradictory' to her rise in power and notoriety, didn't suit a 'warrior' of a boss like her. Yes, these sort of delicate 'clothes' were far too dainty, and deserved only to stay in the bedroom, but for the right people--one or two molls before her precious Chiyo-chan, and especially including him now--she could eagerly slip into something much more comfortable, much more delicate, something that belonged to sinful royalty and shameless front-page celebrities. 

And the remaining two pieces of her sinfully black lingerie? A negligee that was so thin and sheer that her nipples poked through and stood erect from the material caressing her hefty flesh, and a pair of ebony silk panties that had the naughty caveat of having the crotch ripped open, then stitched to ensure that the undergarment remained crotchless. It was for ease of access, after all; fingers wouldn't have to waste precious seconds tugging the undergarment down to get at her honeypot, and her lover's tongue, fingers, and phallus could slip in with utmost simplicity~

The Breaker Queen's eyebrow perked when she heard her cream-clad ladyboy praise whatever gods he worshipped in his 'Tokyo-talk'--she caught enough that whatever name with '-sama' at the end was a deity. "Hmm, you don't need to pray anymore, toots~" She kicked the bedsheets down to the foot of the bed, before she leaned against her massive pillows, propping herself against the bed-rest, putting herself on display for him. "Though, seeing your little man trapped in your pretty little panties is starting to offend me..."

She loved how he stammered and hurried, tugging his pre-stained undergarments down to expose his rigid manhood; stiff, firm, pre-cum drooling from the slit... she was glad that he was somewhere in the middle in terms of his length. A stud way before him was too thick and long for her--he was then found floating in the harbor for nearly tearing her open. Another boy-moll was tiny-dicked and barely satisfied her--so he was shipped off to the East Coast for her sadistic confidant Sam to abuse. And the ladies--sure, they were a nice break, a sweet distraction, but a proper and satisfying dick was so hard to find, until he came along...~

"Mmmm, looks good enough to eat~" She cooed delightedly. "Now, get over here, and stick it right in me...~!"

The order genuinely surprised her cute moll. "...Right away? No rubbers or pills, boss-man?" He questioned, even as he approached and got onto the bed before her, the tip of his manhood directed at her well-framed pussy.

"None. Not this time, Chiyo-chan." Her crimson eyes met his chocolate browns. "I'll let you in on a secret, toots. I want a successor to my name, to my family."

"R-really...?" Chiyo settled himself closer, his cock brushing up and rubbing against her nethers, the soft bush framing her pussy tickling that cock-meat of his. 

"Mmm, yeah. All of my lieutenants are handy--Gracie, Chauncey, Frank, even Sam--ooh God, Sam... I trust them all to run the empire if things get hairy and go south, but I want to keep my successors... 'in the family.' Get my drift...?" Even as she boldly bared herself to her favorite, she couldn't hide the flushing of her cheeks... and the thoughts that started to invade her mind only got her folds dampened once more. "I want YOU, to fill me up and gimme your all...! Fill and fuck me, until I'm damn sure you knocked me up with a kid or two!"

"Ahh...~! Of course, boss-man! Anything for you...!" His lips claimed hers lightning-quick, his hips jutting forward and welcoming itself back into that familiar warmth between her legs. "Mmnph~! I-I'm honored, truly...!!"

"Ahn--yeah...! So you better not pull out and splatter that jizz all over me... because you're trying to be 'polite'!" Her ebony-coated legs wrapped around his waist, urging him to fall into her chest, to hold onto her as he started his pace. "Mmnph--aah--you waste a SINGLE drop of that sweet cum outta that dick of yours, and you'll be sleeeeeping with the--fiii--"

"Anything...! Anything for you, boss-man...!!" His fingers sank into her shoulders, hands holding onto her from behind as he bucked his hips in and out. "Put a gun t-to my head--and ride me--aaah--until I f-fire on empty--and I'll just ask 'how many more l-little mouths do you want?'!!"

"Mmnn--good!! My loyal doll--my sweet loyal doll...!!" Her fingers gripped his cheeks, lips claiming his in a silent assertion of her command.

The intermingled couple continued rocking the bed, no more words needing to be said as her body rocked beneath her lover's. The Queen's legs squeezed tighter around his waist, a sheer-coated band that tightened around her ladyboy and urged him to thrust deeper, not faster--not yet...! She waited as his hands moved away from her shoulders to root themselves into the bed's headboard, before her fingers reached around and sunk her digits into his shoulders, digging her fingernails into that supple flesh of his.

Chiyo's gasps filled the room, matching his Queen's sounds of pleasure, as he continued railing into her. Her little encouragements, from the nails along his skin, to the squeezing of his waist and hips, and even the feel of her lips claiming his exposed neck and letting her cries melt into his skin, it all served to ease her favorite to continue; he couldn't yield for even a second when she got this possessive of him. Whether riding him like a cowgirl breaking a beast of burden in, clapping his wrists in cuffs to her bedframe to have him as she wishes, or making her demands known even when being pinned down by him, she was firmly in control of him...

And while it didn't look like it would be changing anytime soon, the brunette moll had no qualms about that.

He pumped his hips faster, letting the lovers hear the sound of their sexes clapping in moistened excitement, engraving the sensations, the scents, the sounds into their memories. To crave her clingy hands digging as deep as she could into his smooth, toned flesh, to hear the escalation of her satisfied cries fill the bedroom, to relish in the tightening of her inner walls along his driving cock--he couldn't stifle his own cries just to hear her pleasure any more.

And the Queen, always so cordial and simple with almost everyone else who wasn't family, equally drank in her favorite's cries. Always trying to be a gentleman, she could surmise easily; her hand moved from his shoulder to grab that smooth jawline, and crashed his lips on his, letting their moans mingle and their tongues dance together, a waltz of saliva and muscle that spiked with a cresting shriek from the Queen, succumbing once more to orgasm and coating her moll's cock with her warm honey-glaze cum.

"Aaahh--do it--!! DO IT...!!" She begged firmly, eyes meeting his with a fiery gaze that spoke both business AND desperation, her tone reeking of the latter. "Don't be gentle with me--fucking knock me up!!" To feel his hands pull her body lower on the bed, her head resting on only one of her pillows proper, and she could feel his hips slam harder, their sexes clapping lewdly to her ears! "You deserve this too--fill me up, you beautiful bastard!!!"

With his lips suddenly claiming her neck as his, and a deepened moan of satisfaction on her skin, her favorite had hilted completely inside her heated sex. No bothersome rubbers, no bitter pills, no alternative contraceptives--a hot, raw torrent of thick, creamy seed had shot deeply in her starved 'mother's mouth'. And the volume he was filling her with--she could've sworn that the other night she had gotten a nice dollop of 'cream' out of him as a late-night treat. How could so much have remained inside those taut balls of his??

"Ahh... FUCK, Chiyo-chan..." She sighed contently, a hand reaching to his cheek. "If THIS doesn't put a bun in my oven, then I'LL be surprised~"

Chiyo's quickened gasps and grunts were petering to a more manageable pace, his breathing airy, his eyes fluttering and batting the lusty haze out. His hands, though, remained at the sides of her head, his vision taking only to the blushing beauty below him, looking up at the moll who had just crossed that line with a coy smile on her soft lips.

"Mmm... I-If you a-aren't, somehow... then I'll just h-have to do it again... and again... And again...!" Chiyo pledged, breathing faintly the complete scent of the Breaker Queen. "A-as many times as it takes, until you're satisfied, boss-man...!"

"Damiana."

He looked down to her, eyes lost in her crimson gaze and much brighter cheeks.

"Only my folks, and Sam, are allowed to call me by my name. Those who're my closest and most dearest to me..." She breathed him in in turn, hands reaching to pull him closer, to let her heartbeat be felt, to keep him atop of her to keep his semen in and swimming towards their intended destination. "And now YOU'RE in that close circle, too, Chiyosuke."

"Ah--I-I'm not worthy, b-boss-man--"

"Well, that's not YOUR decision to make, toots." She iterated firmly. "And don't gimme none of that 'honor' bullshit your people say they boast--you got a secret to keep, now. If you so much as spill my name to ANYONE below me, I'm snapping that skinny little neck of yours, capiche?" 

"Y-yes--capiche, boss-man!!"

"Wonderful. And I would hate to have to do that--you're the full package, Chiyosuke." She licked her lips, and claimed his lips in a hungry kiss. "And I don't want to break my most precious possession... especially as it'd mean my successors would have to grow up without their _daddy_ around... Do you understand, doll?"

"I-I understand, boss-man." He nodded, before he caught her giving him quite the accusatory glare. "Ah! I-I mean... Damiana."

Her features softened to a gentle smile. "That's more like it, Chiyosuke."

She would breathe in deeply, then assert her strength to roll him onto his back while she straddled him, still connected by their sexes. Strong, and dextrous, with not a drop spilled out of her over-filled pussy. Those digits would grip his toned hips, while her piercing ruby gaze met his intoxicating chocolates. Even with the heart-to-heart, their hearts both raced at the prospect that was more than 'business as usual'~

"Now, I ain't doubting that that did the trick, but... Just to be sure... It's time to keep this shindig going all night~!!"

**Notes for the Chapter:**

> (Perhaps, in these end notes, I'll time-stamp these as various points in the Queen's life.)
> 
> (In which the Breaker Queen has been the head for many years, and used to getting things her way~)  
> (And yet, at the point in her life where she's thought long and hard about keeping her reign 'in the family'...)  
> (Age: she'll never tell anyone~)


End file.
